Dichloromethane → Pyridine, 4,5-bis(chloromethyl)-2-(trifluoromethyl)-

HRID 225542Notes

Reaction equation

HRID 225542 reaction equation
OC[C:3]1[C:4]([CH2:13]O)=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][CH:8]=1.S(Cl)([Cl:17])=O.Cl[CH2:20][Cl:21]>>[Cl:17][CH2:13][C:4]1[C:3]([CH2:20][Cl:21])=[CH:8][N:7]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:5]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 586879226-(Trifluoromethyl)-3,4-pyridinedimethanol

Product 1

HCID 57753353Pyridine, 4,5-bis(chloromethyl)-2-(trifluoromethyl)-Yield 66%

Procedure

To a room temperature suspension of 2.5 mmol (5-Hydroxymethyl-2-trifluoromethyl-pyridin-4-yl)-methanol (CAS: 765298-25-7) in 3 ml dichloromethane was added dropwise 12.5 mmol thionylchloride. After 1 hour, the reaction mixture was evaporated in vacuo. The residue was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a light yellow oil (66% yield). MS (m/e): 243.0 (M−H, 100%)

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-072a9ed33eb64a33bf047e4c9a85590f
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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